It was a reasonable question posed by members of the Alex Thomson Racing team as we sat around a backyard picnic table in Newport, R.I. for a Memorial Day dinner of ribs and beer.

“Well, if by sailing you mean going on a cruise to the Bahamas or one of those architectural boat tours around the city, then yes. But any sort of traditional sailing? No, not exactly.”

The mostly British crew all kind of smirked and glanced at each other, most likely refraining comment out of politeness towards the neophyte journalist, who the following morning would join five of them in delivering the 60-foot long HUGO BOSS racing yacht to New York City in advance of The Ocean Masters New York to Barcelona Race, which begins on June 1st. While that journey will take the boat’s two skippers between 12 and 14 days, this trip was expected to last about 24 hours or so. Simple enough for a rookie sailor, right?

“It’s like never flying and going up in a fighter jet,” Nicola Breymaier, whose husband Ryan will be one of the boat’s two skippers for the delivery and upcoming race, says, breaking the silence. “Or like learning to drive in a Formula One car.”

In addition to the warning, I’m given an official team kit (a jacket, waterproof sweater, wicking short-sleeve polo shirt and both waterproof pants and shorts) plus an anti-seasickness medication from Europe that I’m advised to take two hours before boarding as a precaution.

I arrive at Newport Harbor at 9:30 on Tuesday morning, as rig manager Will Jackson effortlessly scales the boat’s 92-foot mast as part of the crew’s final preparations. Just five days earlier, the team had finished a strenuous structural repair of the key part of the vessel, which had arrived in town in two pieces. The boat, which is falls under the IMOCA 60 classification (for 60-foot-long yachts) has been sailed around the world in numerous major events, including the 2012-13 Vendee Globe, a single-handed race that takes place every four years. Unlike the America’s Cup, a series of team-based short races, these boats are designed for short-handed endurance events, where one or two skippers sail unassisted for long ocean distances.

Made mostly of carbon fiber, every racing yacht in this class is built for speed, yet must be structurally sound enough to withstand the rigors of the most treacherous ocean conditions for months at a time. Other than the navigational and electrical system, the boat’s small hull below deck is bare bones, with no bed or toilet. There is a foam pad on the floor and a makeshift bunk area designed on top of supplies. I start to realize that this isn’t exactly going to be a comfort cruise.

Just before we set sail around 11:30, the boat’s operations manager, Ross Daniel, summons me to the massive grinder in the cockpit. He shows me how to position my hands opposite his and together we hoist the boat’s main sail. Even with the boat docked and no wind, it’s a decent 30 seconds of upper-body effort, one that the boat’s two skippers will have to do repeatedly over the course of the trip.

The weather seems perfect to me as we head out of Newport, a sunny day with temperatures in the mid 70s. With only slight winds – and ones pushing in the opposite direction of our destination rather than towards it – it’s not as ideal for the guys trying to sail the boat. As Daniel gives me a safety tutorial during out placid exit out of the harbor, the potential risks of the trip become even more apparent.

“If someone falls overboard, the first thing we do is yell ‘Man overboard!,” he instructs me, as we weave along the small corridor in the back of the boat. He shows me which secure ropes are OK to steady myself on (the waist-high ones attached to the carbon-fiber body) and which ones aren’t (the ones attached to the sails or winches) as well as how to stay crouched when walking towards the front of the deck. As someone who has enough trouble not tripping on New York City sidewalks, I’m not extremely confident in my ability to stay sturdy on a constantly shifting ocean vessel. It’s at this point that I feel no shame in being the only person on the boat to ask for a life jacket to wear on top on my racing kit.

While I grip a chunk of the side of the cockpit for balance, Ryan Breymaier sprints up to the front to untangle a sail that has been caught on small ropes on the left side of the boat. The 38-year-old Annapolis, Md. native bounces around the boat with the agility of a Nintendo game character, a spry confidence that comes with two decades of experience as a sailor.

The boat’s other captain, 43-year-old Pepe Ribes, started sailing at seven in his hometown of Benissa, Spain. A veteran of four around-the-world Volvo Ocean Races, I ask Ribes if he’s started teaching the sport to his own 3 1/2 year old son.

“He’s too young,” Ribes says. “I will wait until he is five.”

With no bathroom facilities on board, I ask Daniel exactly what the protocol is when nature calls while on the boat. His full explanation can be seen in the video below, but with a potential 24 hours of sailing ahead of us, I begin to steel myself mentally at the prospect of having to use “the bucket.” (Thankfully, this is one sailing ritual I will manage to avoid).

Everything is going pretty smoothly for the first few hours of the journey as we approach the coast of Block Island. If anything, the most inconvenient part of the trip for me so far is that I can’t seem to rid my head of an alternating medley between Billy Joel’s “Downeaster Alexa” and “Boats & Hoes” from the movie Step Brothers. That nautical mental mashup is interrupted by Breymaier and Ribes’ grinding and tacking the sails (basically, adjusting from one direction to another to take advantage of the wind). The current conditions are making it difficult for the boat to get a steady momentum so the men are trying to zigzag with the wind to stay on course. This means doing a lot of physical labor without much speed in return.

“I always tell people that the worst part of the whole thing is when it’s light air,” Breymaier says later. “You saw today when you’re really working hard and not going anywhere. Sometimes when you’re really working hard and going nowhere, you realize that there can be someone five miles from you and they can have plenty of breeze and be doing four times your speed. Then you’re not too pleased about the whole thing.”

The push and pull continues over the next few hours as we move off the southeastern end of Long Island near sunset. It has started to cool significantly and I’m starting to wonder if my three layers will be enough to keep me warm overnight. Even when we do pick up a steady bit of momentum, Ribes and Breymaier are never idle. As the boat coasts along, they keep themselves busy by threading rope or checking the upcoming conditions on a specially equipped iPad.

Pepe Ribes and Ryan Breymaier

The motion of the boat didn’t seem to bother me during the day, but after we hit nightfall, I’m starting to feel a little more uncomfortable. That fact that thunderstorms could be in the forecast ahead doesn’t exactly help either. I head inside the darkened hull, which is illuminated only by our individual headlamps and the glow of the navigational system’s monitor. Despite the fact that every wave sounds like a pool ball bouncing off the side of the boat, I’m surprised at how easy I’m able to fall asleep for an hour or so.

By the time I wake up, I can feel that the boat has picked up significant velocity. I head outside, where the weather system has finally given us some assistance. We’re traveling at 18 knots (about 20 mph), the fastest rate of the trip. With the freezing water spraying around and a slight disorientation from the darkness, we might as well be going 100 miles an hour. It’s almost unfathomable that the yacht can actually get up to twice this speed during some ocean races.

“Now we’re finally sailing!” Jackson yells, possibly noting the sheer discomfort on my face. After about ten minutes in the cockpit, I take shelter back inside the hull. We’re now about 14 hours into the trip and although I’m not expressing this to anyone else on board, at this point, I’m feeling like a kid at a sleepover who wants his parents to pick him up early. At no point do I ever feel endangered, but there’s something about being in a vulnerable state in the middle of so much darkness that I’m not enjoying.

That’s obviously something that experienced sailors overcome pretty early, especially world-class ocean racers. And sure, it’s probably a lot easier to let your mind wander when you aren’t tasked with trying to do ten exhausting things at once, not to mention managing alternating 90 minute sleep patterns like Breymaier and Ribes will be forced to do during the Barcelona race. But while I knew I’d be getting off the boat at some point in the next 12 hours, I wondered how these guys are able to mentally conquer being on here for journeys that sometimes last up to three months.

“If you imagine being on the subway for 100 days, that’s pretty much the same difference,” Breymaier explains. “Imagine we’re down here shaking around going in a straight line. It’s the same thing, except for when you go upstairs you have a whole world of fun to play with. It’s like camping out on the subway. It gets to be – you can imagine after a while – it may as well be like your apartment. You’re there for so long you create a rhythm of life that’s as normal as possible.”

While we were initially expecting to arrive in Manhattan around late morning on Wednesday, the extra speed we picked up overnight winds up accelerating our arrival into the city. As the first signs of daylight started to emerge around 5:30 a.m., I hear someone on deck yell that we are about to approach the Verrazano Narrows Bridge. I emerge outside and feel immediate relief to see Coney Island in the distance to the right and Staten Island off to the left. For the next two hours, we roll through a chilly New York harbor, as I point out my neighborhood of Red Hook, Brooklyn to the crew on one side and get a closer look at the Statue of Liberty than I ever have before. It’s worth the previously jangled nerves.

Next to me, Ribes takes in the landscape with a satisfied grin, even snapping a few photos with his iPhone. Even though this trip is basically his equivalent of routine batting practice, there is still a palpable joy in the completion of a successful voyage. I can only imagine how much that multiplies when he reaches a destination that takes 12 times the duration and effort to get to.

“It’s a lot of hard work,” he’d said the previous afternoon. “But it beats working in an office.”

For The Win got an exclusive ride along as the Alex Thomson Racing team delivered their world-class racing yacht from Newport, R.I. to (…)

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